Diary of a Horny Student Ch. 21

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A brief detour: The history of Kelly, Sandy, and Don.
14.4k words
4.8
13.8k
12

Part 21 of the 33 part series

Updated 12/29/2023
Created 04/01/2022
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21

Kelly was turning 30 years old. Like many other women her age she had hopes and dreams of what her third decade might bring, but what Kelly definitely didn't expect when she turned 30 was to be a single mother for the second time.

Kelly met her first husband, Roger, in college, a friend of a friend who stepped in one night when her planned date bailed on her. Kelly didn't get out too much, always head down in her studies, and she had gone all out for this date. She did her hair, wore her tightest pants and her nicest blouse, even borrowed a push up bra from her roommate to make sure all her assets were on display.

She was excited. She had met her date at a party a week or so ago, a party she almost didn't go to, save for the urging and encouragement of her best friend Sandy. The opposite of Kelly, Sandy was a social butterfly, far more interested in the more enjoyable side of college life. That's not to say Sandy wasn't a good student though. She was the gifted type who could party through the weekend and not remember any of it, while also being ready to go for an exam on Monday. Sandy and Kelly were inseparable, and Sandy had been there to help Kelly broaden her horizons ever since day one.

Sandy and Kelly met the night of the first formal dance at their college. 18 years old, and away from home for the first time, Kelly was excited to share a luxurious night out with her boyfriend. High school sweethearts, they were both shy virgins when they got together. They made love for the first time one summer night after graduation, and even though it was short, and not entirely pleasurable for Kelly, it excited her to no end. She was now a sexual person, a woman, and she thought she had found her person. They had shared this intimate, intense experience, and she was sure the connection they now shared would carry them into many years of love.

Unfortunately what it brought was only a couple more awkward sexual experiences together in between shifts at their respective summer jobs and an uncertainty about where their relationship was headed.

Their last night together had been enjoyable enough, seemingly for both of them.

"Do you think maybe you could suck my dick next time?" He asked as she climbed off his softening penis, and back into the passenger seat of his car.

Kelly was taken aback. Admittedly she was a little hesitant (one might even say afraid) of putting a hard penis in her mouth, of giving up that much control, but as she looked down at herself, plump tits still exposed and red from sucking, bunched up skirt barely covering her wet, swollen pussy, she couldn't help but wonder what she had done wrong. She had taken his cock inside her and milked him with her body until he exploded, and didn't even complain or feel cheated that she once again hadn't cum herself. But apparently he was still feeling unsatisfied.

"Uh, sure..." she said, trying to organize all the thoughts swirling in her head, "...I don't see why not."

There wouldn't be a next time before they both left for college, and Kelly would be lying if she wasn't slightly relieved. Not so much because she didn't want to suck his dick, she was willing to try it if that's what he wanted, but more so because something felt off. She couldn't put her finger on what it was, but it was something.

College started, and Kelly began focussing on her studies. She did her best to talk to her boyfriend as often as possible, but as these things go, nightly turned into twice a week, which turned into weekly, which turned into bi-weekly. The dance was coming up however, and Kelly saw it as the perfect opportunity to rekindle things. They had both been focused on school (or so she thought), but the dance would be the chance for them to focus on each other, and she was ready. If he wanted his dick sucked, she was going to suck his dick.

Having a boyfriend who went to a different school, Kelly wasn't on the market, but she wasn't dead either. She still had needs, and as she was a great student, her regular self-pleasure sessions became erotic study sessions. She touched herself to a wide array of "research material" she found on the internet, and as her pussy began to develop a pavlovian response to the images of a hard cock being loved on by the mouth of a beautiful woman, she began to understand it. To want it.

She was looking forward to it. She fantasized about feeling the spongy head with her tongue, about feeling his hard shaft slide between her lips. She wondered how much of him she'd be able to take in her mouth, what she'd be willing to do when it came time for him to shoot his load. She wanted nothing more now than to suck her boyfriend's cock, and she was going to rock his world at the dance.

Then the phone call came.

Sandy was on her way to the showers, the first step in preparation for what she knew was going to be an amazing night. She was getting ready to go to the formal dance with her boyfriend Don, and she wanted everything about her look to be perfect. Sandy and Don had met at the local bar the first week of college, and they had been joined at the hip ever since. Or, more specifically, joined at the crotch. Sandy was no virgin when they met, she had her fair share of fun in high school, but there was just something different about Don. A different feeling. A different energy.

Don was a junior, and wasn't looking for a new relationship. He had just had his heart broken and was out with some friends, looking only to hang out and have drinks, when across the room his eyes fell on the most gorgeous thing he had ever seen in his life: a wild mane of dirty blonde hair; a smile that could only be described as lusty; a pert, tight butt, and two, large, supple breasts encased in a tight, low cut shirt, boiling over with deep cleavage.

Suddenly he found himself wondering what those breasts felt like in his hands, what her nipples tasted like, what she sounded like when she orgasmed. He found his way over to her by the bar, where she accepted the drink he bought her with a smile. By the end of the night he found himself balls-deep in her pussy, her lovely body bent over the hood of a car. He got to feel those breasts, taste those nipples, and hear those orgasmic sounds as she spasmed around his hard cock.

Don's balls began to boil, and as he announced he too was going to cum, he only then realized they were too caught up in their lust to remember a condom, but it was no matter; without missing a beat after his climactic announcement, Sandy breathlessly offered three words back: "In my mouth." This sent a surge to his balls, but it was the fourth word she choked out after catching her breath that sent him careening over the edge: "...please."

His cock stiffened harder than iron, and in almost a single, smooth motion, he slipped his cock out of her pussy, and Sandy melted down to her knees, taking him into her mouth. Don felt one hand on his balls and another gripping his hip, and after no more than three or four bobs of her head, his whole body tensed, and this girl he'd just met received a mouth full of hot cum.

She looked in his eyes as she swallowed, and suckled gently on his softening tip as his breath came back to him. They both smiled. They both laughed. They both knew this was something special.

That night was only the first of many that Sandy and Don spent together. That night had been erotic, electric, dirty and explosive, which is exactly why Sandy put the breaks on the physical stuff for the next couple weeks. Don's cock was perfect for her, and he had made her cum harder than any man had at that point, but she wasn't just looking for a quick fuck from this guy--she wanted to see if their chemistry extended outside the bedroom as well.

Don was a total gentleman on their much more chaste followup dates, never pushing, never pressuring, just happy to spend time with Sandy and get to know her. It was this chivalry, on top of the fact that he was legitimately an amazing guy, that sent her home soaking wet, where she would attack her dildo with purpose, cumming long, hard, and loud into her pillow.

They both knew what was in the air the night they went to watch their mutual friend play basketball for their college team. Few words were said, but few words were needed, as the smiles on their faces spoke volumes. After saying goodnight to their friends, they drove silently back to Don's apartment, slipped into the bedroom, and made long, slow, passionate love throughout the night.

This time when Don gasped, and his balls pulled tight to his body, there would be no pulling out. Sandy's legs gripped him closer than ever, and she felt every pulse of his spasming cock as her body milked his cum into hers. Breath left her body and with Don's bare cock still pumping inside her, Sandy began to cum as well. It would be the first of many barriers brought down between them, and soon they would begin to explore every corner of each other's desires and fantasies, something they would continue to do deep into their eventual marriage.

Sandy was excited about the dance because she was planning to explore one of those corners of fantasy that night--she wanted everything to be perfect, because she was going to give Don her anal virginity. She had had fingers, toys, even the stray tongue in there in the past, but she'd never committed to letting a cock penetrate her ass, and that night she was ready to give it to Don.

As she made her way toward the showers she thought about the evening, about the act. For the first time in a while, she was nervous. She practically knew Don's cock front to back at that point, but still, anal was something totally new for her. His dick was long, and it was thick, and her ass was very tight. She wondered if he'd be able to fit it all in; what it would feel like for him to fuck her; what it would feel like when he came.

A drizzle of arousal began to trickle down into Sandy's loins as she entertained the thoughts, but she was suddenly brought back to earth by the faint sounds of sobbing.

Rounding the corner of the hall into the common area, she saw a cute brunette curled up on the couch, her head in her knees, doing her best to muffle the sounds of her sadness.

"Hey...are you ok?" Sandy inquired. With a long sniffle and a start, the brunette picked her head up, and Sandy and Kelly met for the first time.

The two clicked instantly, sitting and talking as Kelly vented her frustrations and sadness about her boyfriend. Not only would he not be coming to the dance, but he was breaking up with her.

"He said we had grown apart," Kelly said through sniffles, "but I could tell it was something else. I knew there had been something else for a while, so I kept pushing, and finally..." she trailed off.

"Was there someone else?" Sandy asked, placing a comforting hand on Kelly's knee. Kelly nodded.

"And there had been for a while. Some skank from our high school - he had been cheating on me since before we even left for college!" Kelly said angrily,

"Oh, sweetie, I'm so sorry!"

"And I know why, too--Christ, it all makes sense now--I mean I had...I mean we had...a few times, but I never...and he found some skank who WOULD!"

Sandy was admittedly a little confused, but also found Kelly's shyness very cute. "I'm not sure I follow, sweetie, what are you--"

"He broke up with me because I wouldn't suck his dick." Kelly just blurted out.

"Oh!" Sandy said, seeing things clearer now. "So you never..."

"No, we DID, and that's the thing! We had sex! Multiple times! And he still wasn't satisfied! And I mean neither was I, but you didn't hear me complaining..." she said with a chuckle as she wiped her nose.

"So wait, he never made you cum?" Sandy said, Kelly's eyes going wide at the unexpected candor of her language.

"Nope." Kelly shook her head

"Never? Not even doing other stuff?"

"Nope."

"So let me get this straight," Sandy began, taking all the info in, "this guy, who never made you cum, ever, but who got to experience all the pleasures your body had to give him, broke up with you because you wouldn't put his sad little pecker in your mouth?"

"Pretty much," Kelly said, eyes wide again.

"Well I say he did you a favor--good fucking riddance, girl! There are plenty of bigger, better cocks, mouths, fingers, you name it out there just dying to make a girl like you cum till you pass out, and now you are free to go hunting!"

Kelly laughed out loud this time at Sandy's lewdness. She couldn't tell if it was a put on to cheer her up, or just the way she always was, but either way, she liked it. It was shocking, but she liked it. She liked Sandy. And she could tell that Sandy liked her back.

"Funny thing is," Kelly said after a pause, "I was going to do it tonight--after the dance--I was gonna suck the life out of him. But now I'll just be home by myself like every other night."

Now it was Sandy's turn to be surprised at Kelly's language, but it gave her an idea.

"Listen...you've got a dress, right? You were already planning on wowing everyone in the room, right?"

"I guess..."

"Well there's no reason not to just on account of that asshole--why don't you come to the dance with me and my boyfriend Don?"

"I could never...I wouldn't want to impose..." Kelly said, waving her off

"It's no imposition at all! It'll definitely get people talking, and trust me, Don will love walking in with two gorgeous ladies on his arm, that's for sure."

They both laughed, and Kelly considered the offer.

"Are you sure?" She said, a strained look on her face.

"Absolutely. You can't walk in with us, and if you happen to walk out with someone else...well then all the better, right?" Sandy bounced her eyebrows seductively.

Kelly took a long pause and then a big smile pulled at her lips. She nodded enthusiastically in agreement. The two of them shared an excited hug.

"Perfect," Sandy said as she pulled away, her smile matching Kelly's, "Now you go get ready, and 'll start telling all the guys you're looking to suck some cock tonight!"

"SANDY!" Kelly yelped, and the two broke into laughter.

When the two new friends finally calmed down, they said their temporary goodbyes, and Sandy smiled as she watched Kelly practically skip down the hallway toward her room. Sandy sighed with a smile and resumed her journey to the showers.

The hot water cascading down her tight, young body, Sandy thought about Kelly, and what the night might bring. She liked Kelly, and looked forward to spending more time with her. She was happy Kelly's boyfriend broke up with her, as if not for that, the two never would have met. She thought about how stupid Kelly's boyfriend was, giving up a girl like that over a blowjob. It's true Kelly had a great body, slim waist with a nice big flare at the hips, two plump breasts perched pleasantly on her chest, and it's true that Sandy took notice. She appreciated the female form as much as the next person, and knew that whoever got the next crack at Kelly was a lucky man. Lastly she thought about her original plans, probably now dashed. She didn't care. She might not be losing her anal virginity that night after all, but at least she did her good deed for the week and made a new friend in the process.

"So she's never sucked cock before, but she wants to now?" Don said into the phone as he got dressed. Sandy was telling him the new plan for the evening, and all about the new friend she just made, but of course, as was his way, it seemed like Don had selective hearing.

"No, no," Sandy said back as she took in her freshly showered body in the reflection of her full-length mirror, wet hair up in a towel, "well, I mean, yes, I think, but you're missing the point, as usual!"

Sandy wasn't necessarily what you'd call a vain person, but she knew she had a good body. Tight and wide in all the right places, with two big, luscious tits that seemed to match her ass in the disregard for the force of gravity, she had what men liked. And some women, too. Her tits were definitely a major attraction, and always received a lot of attention, whether from eyes, hands, lips, or, on very special occasions, cocks.

She smiled at her reflection, thinking back to a night not that long ago when she had been on her knees in front of this mirror, her thick breasts wrapped tight around Don's thrusting cock. She knew how much the boys loved her tits, how badly they wanted to slide their pricks between them, and that's why she reserved that act for only the most worthy--for the boys who earned it. And good God, had Don more than earned it.

She just smiled, and thought about how lucky she was to have found him, and how important to her his pleasure was, because her pleasure was equally important to him. When he began to grunt and shake, Sandy cooed and encouraged him and with a gasp and a shudder, hot, white streams began to spurt up from her tight cleavage.

If fucking Sandy's tits was rare, cumming between them was almost unheard of. In fact it had only happened one other time, with Rich Genoveraci the summer before college, and that was only because he was so excited to get between her globes that he couldn't control himself. It was fine with Rich, he was a good guy, she wasn't mad, but it was different with Don. She wanted him to cum on her. He could cum however he wanted, wherever he wanted, and she wanted him to know that.

As Don began to cum, Sandy's eyes darted to the side, and caught her reflection in the mirror. Boy what a sight: wild mane of blonde highlights, the sweet curve of her back into her perfect ass, big breasts pressed together, Don's considerable cock cresting out from between them over and over, spurting wildly...she liked it. She liked it then, she liked it earlier when she got to watch herself cum while Don fucked her from behind, and she liked it moments later when he ate her still soaking pussy to another orgasm, his cum still glimmering on her chest as he did so.

"Maybe next time I'll let him cum on my face," she thought as she took in the final ebbs and grunts of Don's orgasm, "I bet that would be even hotter to watch."

She would, and it was.

"I don't know, Sandy, I thought tonight was going to be about us?" She could hear his disappointment through the receiver clear as day.

"I know, baby, but she needs a friend," Sandy said with a mock whine, "and besides, think about it this way: you get to walk into the dance with two absolute smokeshows on your arms, go home with at least one of them, you've done a good deed for the week, and you get to end the night in bed next to your very...very...appreciative girlfriend..."

There was a long pause on Don's end, and Sandy smiled--she knew she had him.

"...what do you mean I get to go home with AT LEAST one of you?"

"Don!"

"Ok, ok! Yeah, fine, let's do it."

Sandy smiled once again. "Thanks, baby, you're the best. Now pick us up at 8 and try not to drool TOO much when you see what you're in for tonight."

Sandy hung up the phone, took one last look at her perfect, nude body, smiled, and started getting dressed.

Don leaned against the hood of his car as he waited for Sandy and Kelly to come down. He had agreed to let Kelly join them at the dance, but truth be told he was a little put out to have to deal with a third wheel tonight. He was sure she was very nice, and he was happy to help, but he and Sandy had been looking forward to this night for a long time. From the innuendos Sandy had been throwing his way he knew she had something special planned, but now those plans were probably scrapped. Gone too was his hope to maybe get a little road head either to or from the dance. He just hoped this Kelly person appreciated how all of her blues went straight to Don's balls instead.

He had just put a cigarette between his lips when the door to the dorm opened up and two absolute visions cascaded down the stairs.